GB1072118A - Amides of aminopropionic acid - Google Patents

Amides of aminopropionic acid

Info

Publication number
GB1072118A
GB1072118A GB4679863A GB4679863A GB1072118A GB 1072118 A GB1072118 A GB 1072118A GB 4679863 A GB4679863 A GB 4679863A GB 4679863 A GB4679863 A GB 4679863A GB 1072118 A GB1072118 A GB 1072118A
Authority
GB
United Kingdom
Prior art keywords
amide
stearylamine
acid
methylation
amidation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB4679863A
Inventor
Kurt Hoffer
Rudolf Kessler
Urs Dollberger
Rolf Gross
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sandoz AG
Original Assignee
Sandoz AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to CH1414962 priority Critical
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB1072118A publication Critical patent/GB1072118A/en
Application status is Expired legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

Abstract

Novel basic amides are prepared by first reacting 1 to 2 mol of an ester of acrylic acid with a volatile alcohol, at a temperature below 100 DEG C. at which no substantial amidation occurs, with one mol. of primary, secondary or tertiary amine of the formula <FORM:1072118/C2/1> to form an ester-amine which is then further heated with 1 to 2 mol. of a primary, secondary or tertiary amine of the formula <FORM:1072118/C2/2> to form an amide-amine with simultaneous splitting off of an alcohol, said amide-amine being subsequently alkylated, alkoxylated and/or quaternated and/or acylated if desired, one of R1, R2 and R3 representing C12- 24 alkyl or alkenyl, each of the remaining five of R1 to R6 representing hydrogen or C1- 6 alkyl or hydroxyalkyl, A1 and A2 each representing a C2- 6 alkylene radical and each of m and n representing 0 or an integer of from 1 to 6 inclusive provided that at least one represents an integer. Examples describe the preparation of (1) a 1 :2 addition product of stearylamine and ethyl acrylate, amidation of this diester with 2 moles of 1,6-hexamethylene-diamine and either ethoxylation and quaternization, methylation, or propionylation and methylation of the resulting stearylamino-dipropionic acid di-1-aminohexyl-6-amide; (2) a 1:1 addition product of stearylamine and ethyl acrylate, amidation of this ester with 1,3-propylenediamine and either ethoxylation and quaternization, methylation or acetylation and methylation of the resulting stearylamino-propionic acid 1-aminopropyl-3-amide; (3) a 1:1 addition product of stearylamine and ethyl acrylate, amidation of this ester with 1,2-ethylenediamine and either methylation or methylation and acetylation of the resulting stearylamino-propionic acid 1-aminoethyl-2-amide; (4) a 1:1 addition product of stearylamine and ethyl acrylate, amidation of this ester with 1 mole of 1,6-hexamethylenediamine and either methylation, alkoxylation or alkoxylation and quaternization (with monochloracetic acid) of the resulting stearylamino-propionic acid 1-aminohexyl-6-amide; (5) a 1:1 addition product of stearylamine and ethyl acrylate, amidation of this ester with 1 mole of 1-amino-3-dimethylaminopropane and either methylation or carbamidomethylation (with chloroacetamide) of the resulting stearylaminopropionic acid 1-dimethylaminopropane 3-amide; (6) a 1:1 addition product of stearylamine and ethyl acrylate, amidation of this ester with 1 mole of diethylene-triamine and methylation of the resulting monostearylamino-propionic acid amide of diethylene-triamine; (7) a 1:2 addition product of stearylamine and ethyl acrylate, amidation of this diester with 2 moles of 1,3-propylene-diamine and methylation of the resulting stearylamino-dipropionic acid di-1-aminopropane-3-amide; and (8) a 1:2 addition product of stearylamine and ethyl acrylate, amidation of this diester with 2 moles of 1-amino-3-dimethylaminopropane and quaternization of the resulting stearylamino-dipropionic acid di-3-dimethylamino-propane-1- amide with either methyl sulphate or chloroacetamide.ALSO:Novel amino-amides containing a C1- 24 alkyl or alkenyl group in addition to C1- 6 alkyl or hydroxyalkyl groups (see Division C2) are alkoxylated and, if desired, further quaternated or acylated. The amino-amides and their quaternary derivatives may be used as polymerization emulsifiers. In examples a stearylamine - dipropionic acid di - 1 - aminohexyl-6-amide is ethoxylated with up to 75 mols. of ethylene oxide and subsequently quaternized with dimethyl sulphate and alternatively with chloroacetic acid; a stearylamine-propionic acid 1-aminopropyl-3-amide is ethoxylated with up to 30 mols. of ethylene oxide and subsequently quaternized with monochloroacetic acid or alternatively dimethyl sulphate, benzyl chloride, chloroacetamide, glycolchlorohydrin or epichlorohydrin; a stearylaminopropionic acid 1-aminohexyl-6-amide is propoxylated with 2.4 mols. of propylene oxide and subsequently quaternized with chloroacetic acid; a stearylamine-propionic acid 1-aminohexyl-6-amide quaternized with 2 mols. of dimethyl sulphate is added to an emulsion polymerization system containing aqueous sodium bisulphite, vinyl acetate, ferrous sulphate and hydrogen peroxide; and a stearylamine-propionic acid 1-aminopropyl-3-amide methylated with two mols. of dimethyl sulphate is added to an emulsion polymerization system containing aqueous sodium bisulphite, ethyl acrylate, butyl acrylate, acrylonitrile, ferrous sulphate and hydrogen peroxide; the polymer emulsions may be used for treating textiles or paper.ALSO:Novel amino-amides containing a C12-24 alkyl or alkenyl group in addition to C1-6 alkyl or hydroxyalkyl groups (see Division C2) and their quarternary or alkoxylated derivatives are used as levelling agents in dyeing baths or as emulsifying agents in emulsion polymerization systems, to which they impart improved paper sizing properties. In examples the products are used in a dyebath containing 2:1 metal complex dyes, ammonium sulphate, and formic acid to obtain a level dyeing effect on striped dyeing nylon woven material, and in an emulsion polymerization system containing aqueous sodium bisulphite, ferrous sulphate, hydrogen peroxide, ethylacrylate, butyl acrylate and acrylonitrile, this being used to size bleached sulphite cellulose in conjunction with rosin size, aluminium sulphate, kaolin and an optical brightening agent.
GB4679863A 1962-12-01 1963-11-27 Amides of aminopropionic acid Expired GB1072118A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CH1414962 1962-12-01

Publications (1)

Publication Number Publication Date
GB1072118A true GB1072118A (en) 1967-06-14

Family

ID=4398397

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4679863A Expired GB1072118A (en) 1962-12-01 1963-11-27 Amides of aminopropionic acid

Country Status (3)

Country Link
AT (1) AT258875B (en)
BE (1) BE640639A (en)
GB (1) GB1072118A (en)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4664848A (en) 1982-12-23 1987-05-12 The Procter & Gamble Company Detergent compositions containing cationic compounds having clay soil removal/anti-redeposition properties
US8969353B2 (en) 2008-11-07 2015-03-03 Massachusetts Institute Of Technology Aminoalcohol lipidoids and uses thereof
US9006487B2 (en) 2005-06-15 2015-04-14 Massachusetts Institute Of Technology Amine-containing lipids and uses thereof
US9181321B2 (en) 2013-03-14 2015-11-10 Shire Human Genetic Therapies, Inc. CFTR mRNA compositions and related methods and uses
US9193827B2 (en) 2010-08-26 2015-11-24 Massachusetts Institute Of Technology Poly(beta-amino alcohols), their preparation, and uses thereof
US9227917B2 (en) 2012-08-13 2016-01-05 Massachusetts Institute Of Technology Amine-containing lipidoids and uses thereof
US9238716B2 (en) 2011-03-28 2016-01-19 Massachusetts Institute Of Technology Conjugated lipomers and uses thereof
US9308281B2 (en) 2011-06-08 2016-04-12 Shire Human Genetic Therapies, Inc. MRNA therapy for Fabry disease
US9315472B2 (en) 2013-05-01 2016-04-19 Massachusetts Institute Of Technology 1,3,5-triazinane-2,4,6-trione derivatives and uses thereof
US9522176B2 (en) 2013-10-22 2016-12-20 Shire Human Genetic Therapies, Inc. MRNA therapy for phenylketonuria
US9629804B2 (en) 2013-10-22 2017-04-25 Shire Human Genetic Therapies, Inc. Lipid formulations for delivery of messenger RNA
US9840479B2 (en) 2014-07-02 2017-12-12 Massachusetts Institute Of Technology Polyamine-fatty acid derived lipidoids and uses thereof
US9850269B2 (en) 2014-04-25 2017-12-26 Translate Bio, Inc. Methods for purification of messenger RNA
US9957499B2 (en) 2013-03-14 2018-05-01 Translate Bio, Inc. Methods for purification of messenger RNA
US10022455B2 (en) 2014-05-30 2018-07-17 Translate Bio, Inc. Biodegradable lipids for delivery of nucleic acids
US10138213B2 (en) 2014-06-24 2018-11-27 Translate Bio, Inc. Stereochemically enriched compositions for delivery of nucleic acids

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4664848A (en) 1982-12-23 1987-05-12 The Procter & Gamble Company Detergent compositions containing cationic compounds having clay soil removal/anti-redeposition properties
US9006487B2 (en) 2005-06-15 2015-04-14 Massachusetts Institute Of Technology Amine-containing lipids and uses thereof
US9556110B2 (en) 2008-11-07 2017-01-31 Massachusetts Institute Of Technology Aminoalcohol lipidoids and uses thereof
US10189802B2 (en) 2008-11-07 2019-01-29 Massachusetts Institute Of Technology Aminoalcohol lipidoids and uses thereof
US8969353B2 (en) 2008-11-07 2015-03-03 Massachusetts Institute Of Technology Aminoalcohol lipidoids and uses thereof
US9193827B2 (en) 2010-08-26 2015-11-24 Massachusetts Institute Of Technology Poly(beta-amino alcohols), their preparation, and uses thereof
US10117934B2 (en) 2011-03-28 2018-11-06 Massachusetts Institute Of Technology Conjugated lipomers and uses thereof
US9238716B2 (en) 2011-03-28 2016-01-19 Massachusetts Institute Of Technology Conjugated lipomers and uses thereof
US9308281B2 (en) 2011-06-08 2016-04-12 Shire Human Genetic Therapies, Inc. MRNA therapy for Fabry disease
US10238754B2 (en) 2011-06-08 2019-03-26 Translate Bio, Inc. Lipid nanoparticle compositions and methods for MRNA delivery
US9597413B2 (en) 2011-06-08 2017-03-21 Shire Human Genetic Therapies, Inc. Pulmonary delivery of mRNA
US9439968B2 (en) 2012-08-13 2016-09-13 Massachusetts Institute Of Technology Amine-containing lipidoids and uses thereof
US9227917B2 (en) 2012-08-13 2016-01-05 Massachusetts Institute Of Technology Amine-containing lipidoids and uses thereof
US9181321B2 (en) 2013-03-14 2015-11-10 Shire Human Genetic Therapies, Inc. CFTR mRNA compositions and related methods and uses
US9957499B2 (en) 2013-03-14 2018-05-01 Translate Bio, Inc. Methods for purification of messenger RNA
US9713626B2 (en) 2013-03-14 2017-07-25 Rana Therapeutics, Inc. CFTR mRNA compositions and related methods and uses
US9315472B2 (en) 2013-05-01 2016-04-19 Massachusetts Institute Of Technology 1,3,5-triazinane-2,4,6-trione derivatives and uses thereof
US10208295B2 (en) 2013-10-22 2019-02-19 Translate Bio, Inc. MRNA therapy for phenylketonuria
US10052284B2 (en) 2013-10-22 2018-08-21 Translate Bio, Inc. Lipid formulations for delivery of messenger RNA
US9629804B2 (en) 2013-10-22 2017-04-25 Shire Human Genetic Therapies, Inc. Lipid formulations for delivery of messenger RNA
US9522176B2 (en) 2013-10-22 2016-12-20 Shire Human Genetic Therapies, Inc. MRNA therapy for phenylketonuria
US10155785B2 (en) 2014-04-25 2018-12-18 Translate Bio, Inc. Methods for purification of messenger RNA
US9850269B2 (en) 2014-04-25 2017-12-26 Translate Bio, Inc. Methods for purification of messenger RNA
US10022455B2 (en) 2014-05-30 2018-07-17 Translate Bio, Inc. Biodegradable lipids for delivery of nucleic acids
US10286083B2 (en) 2014-05-30 2019-05-14 Translate Bio, Inc. Biodegradable lipids for delivery of nucleic acids
US10286082B2 (en) 2014-05-30 2019-05-14 Translate Bio, Inc. Biodegradable lipids for delivery of nucleic acids
US10293057B2 (en) 2014-05-30 2019-05-21 Translate Bio, Inc. Biodegradable lipids for delivery of nucleic acids
US10138213B2 (en) 2014-06-24 2018-11-27 Translate Bio, Inc. Stereochemically enriched compositions for delivery of nucleic acids
US9840479B2 (en) 2014-07-02 2017-12-12 Massachusetts Institute Of Technology Polyamine-fatty acid derived lipidoids and uses thereof

Also Published As

Publication number Publication date
AT258875B (en) 1967-12-11
BE640639A (en) 1964-05-29

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